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WO2013077406A1 - Dérivé d'amine aromatique, matière pour élément électroluminescent organique et élément électroluminescent organique - Google Patents

Dérivé d'amine aromatique, matière pour élément électroluminescent organique et élément électroluminescent organique Download PDF

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WO2013077406A1
WO2013077406A1 PCT/JP2012/080319 JP2012080319W WO2013077406A1 WO 2013077406 A1 WO2013077406 A1 WO 2013077406A1 JP 2012080319 W JP2012080319 W JP 2012080319W WO 2013077406 A1 WO2013077406 A1 WO 2013077406A1
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carbon atoms
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由美子 水木
裕勝 伊藤
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Idemitsu Kosan Co Ltd
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    • H—ELECTRICITY
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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    • H05B33/00—Electroluminescent light sources
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    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • C09K2211/1025—Heterocyclic compounds characterised by ligands
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    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an aromatic amine derivative, a material for an organic electroluminescence element, and an organic electroluminescence element.
  • organic electroluminescence elements using organic substances are expected to be used as solid-state, inexpensive, large-area full-color display elements, and many developments have been made. ing.
  • an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the light emitting layer. When an electric field is applied between both electrodes, electrons are injected from the cathode side and holes are injected from the anode side. Further, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
  • Patent Document 1 discloses the use of a condensed aromatic hydrocarbon group having two amino groups as substituents as a dopant material.
  • Patent Document 2 discloses a diaminopyrene dopant having dibenzofuran and a combination of the dopant material and an anthracene host material.
  • Patent Document 3 discloses a diaminopyrene dopant having a structure in which a nitrogen atom is directly connected to the 2-position or 4-position of dibenzofuran and dibenzothiophene.
  • the present invention includes an organic electroluminescence device that exhibits high luminous efficiency while maintaining or improving color purity, an aromatic amine derivative that can be used in an organic thin film layer of the organic electroluminescence device, and the aromatic amine derivative. It aims at providing the material for organic electroluminescent elements.
  • the following aromatic amine derivative, organic electroluminescent element material, and organic electroluminescent element are provided.
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 are each independently Hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted trifluoroalkyl group having 1 to 20 carbon
  • L 1 , L 2 and L 3 are each independently Single bond, It is a divalent residue of a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a divalent residue of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
  • Ar 1 is a monovalent residue derived from a ring structure represented by the following general formula (4).
  • X represents an oxygen atom or a sulfur atom.
  • R 11 to R 18 are each independently Hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted trifluoroalkyl group having 1 to 20 carbon atom
  • R 11 to R 18 is a substituted aryl group having 6 to 30 ring carbon atoms.
  • One of R 11 to R 18 is a single bond that bonds to L 1 .
  • R 15 and R 16, R 16 and R 17 and R 17 and R 18 at least one One or a combination may form a saturated or unsaturated ring.
  • Ar 2 is A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or a monovalent residue derived from the ring structure represented by the general formula (4).
  • Ar 2 is, when a monovalent residues derived from a ring structure represented by the general formula (4), out of the R 11 to R 18, one for L 2 It is a single bond that binds. ]]
  • R 18 in Ar 1 is An aromatic amine derivative, which is a substituted aryl group having 6 to 30 ring carbon atoms.
  • a material for an organic electroluminescence device comprising the aromatic amine derivative of the present invention described above.
  • An organic electroluminescence device comprising a cathode, an organic compound layer, and an anode in this order, wherein the organic compound layer includes the aromatic amine derivative of the present invention described above.
  • the organic compound layer includes a plurality of organic thin film layers including a light emitting layer, At least one layer among the plurality of organic thin film layers includes the aromatic amine derivative according to any one of the present invention described above.
  • At least one of the plurality of organic thin film layers includes the aromatic amine derivative according to any one of the present invention described above and an anthracene derivative represented by the following general formula (20).
  • Organic electroluminescence device includes the aromatic amine derivative according to any one of the present invention described above and an anthracene derivative represented by the following general formula (20).
  • Ar 11 and Ar 12 are each independently A substituted or unsubstituted monocyclic group having 5 to 30 ring atoms; A substituted or unsubstituted condensed ring group having 10 to 30 ring atoms or a combination of the monocyclic group and the condensed ring group.
  • R 101 to R 108 are each independently Hydrogen atom, A halogen atom, A cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, A group composed of a combination of the monocyclic group and the condensed ring group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted silyl group.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms, and the organic electroluminescence device.
  • One of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring atom having 10 to 30 atoms.
  • Ar 12 in the general formula (20) is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, and a dibenzofuranyl group, and Ar 11 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fluorenyl group.
  • Ar 12 in the general formula (20) is a substituted or unsubstituted condensed ring group having 10 to 30 ring-forming atoms, and Ar 11 is an unsubstituted phenyl group. .
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the organic electroluminescence device.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a substituted or unsubstituted phenyl group, and the organic electroluminescence device.
  • Ar 11 in the general formula (20) is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • Ar 11 and Ar 12 in the general formula (20) are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • an organic EL element that exhibits high luminous efficiency while maintaining or improving color purity, an aromatic amine derivative that can be used in an organic thin film layer of the organic EL element, and the aromatic amine derivative are included.
  • An organic EL element material can be provided.
  • the aromatic amine derivative of the present invention is represented by the general formula (1).
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1) will be described.
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 are each independently Hydrogen atom, A halogen atom, A cyano group, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, A substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted trifluoroalkyl group having 1 to 20 carbon
  • Examples of the aryl group having 6 to 30 ring carbon atoms in the general formula (1) include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, Fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrycenyl group, benzo [b] triphenylenyl group, picenyl group, perylenyl group Is mentioned.
  • the aryl group in the general formula (1) preferably has 6 to 20 ring carbon atoms, more preferably 6 to 12 carbon atoms.
  • a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable.
  • the 9-position carbon atom is substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. More preferably, the 9-position carbon atom is substituted with two methyl groups.
  • heterocyclic group having 5 to 30 ring atoms in the general formula (1) examples include, for example, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, Quinoxalinyl group, quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazopyridinyl Group, benztriazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, is
  • the number of ring-forming atoms of the heterocyclic group in the general formula (1) is preferably 5-20, and more preferably 5-14.
  • 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothiophenyl group, 2-dibenzothiophenyl group, 3- A dibenzothiophenyl group, a 4-dibenzothiophenyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, and a 9-carbazolyl group are preferable.
  • the substituted or unsubstituted aryl having 6 to 30 ring carbon atoms in the general formula (1) is attached to the 9th-position nitrogen atom.
  • the group or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
  • the alkyl group having 1 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic.
  • Examples of the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopen
  • the linear or branched alkyl group in the general formula (1) preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • An amyl group, an isoamyl group, and a neopentyl group are preferable.
  • the cycloalkyl group preferably has 3 to 10 ring carbon atoms, and more preferably 5 to 8 carbon atoms.
  • a cyclopentyl group and a cyclohexyl group are preferable.
  • the halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a fluoroethyl group, a trifluoroethyl group, and a pentafluoroethyl group.
  • the alkenyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic.
  • the alkynyl group having 2 to 30 carbon atoms in the general formula (1) may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.
  • Examples of the alkylsilyl group having 3 to 30 carbon atoms in the general formula (1) include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group, Triethylsilyl, tri-n-butylsilyl, tri-n-octylsilyl, triisobutylsilyl, dimethylethylsilyl, dimethylisopropylsilyl, dimethyl-n-propylsilyl, dimethyl-n-butylsilyl, dimethyl -T-butylsilyl group, diethylisopropylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triisopropylsilyl group and the like.
  • the three alkyl groups in the trialkylsilyl group may be the same or different.
  • Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the general formula (1) include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
  • Examples of the dialkylarylsilyl group include a dialkylarylsilyl group having two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. .
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • the two alkyl groups may be the same or different.
  • alkyldiarylsilyl group examples include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. .
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • the two aryl groups may be the same or different.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the three aryl groups may be the same or different from each other.
  • Examples of the trifluoroalkyl group having 1 to 20 carbon atoms in the general formula (1) include a trifluoromethyl group and a trifluoroethyl group.
  • the alkoxy group having 1 to 30 carbon atoms in the general formula (1) is represented as —OY.
  • Examples of Y include the alkyl group having 1 to 30 carbon atoms.
  • Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more halogen groups.
  • the aralkyl group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —Y—Z.
  • Y include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • Z include the above aryl groups having 6 to 30 ring carbon atoms.
  • This aralkyl group has 7 to 30 carbon atoms (the aryl moiety has 6 to 30, preferably 6 to 20, more preferably 6 to 12 carbon atoms), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 20 carbon atoms). More preferably, it is 1 to 10, and more preferably 1 to 6).
  • Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Examples include naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • the aryloxy group having 6 to 30 ring carbon atoms in the general formula (1) is represented by —OZ.
  • Z include the above aryl group having 6 to 30 ring carbon atoms, or a monocyclic group and a condensed ring group described later.
  • Examples of the aryloxy group include a phenoxy group.
  • halogen atom in the general formula (1) examples include fluorine, chlorine, bromine, iodine, and the like, preferably a fluorine atom.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • substituents include the aryl group, heterocyclic group, and alkyl group (straight chain or branched chain alkyl group, cycloalkyl group, halogen Alkyl group), alkenyl group, alkynyl group, alkylsilyl group, arylsilyl group, alkoxy group, halogenated alkoxy group, aralkyl group, aryloxy group, halogen atom, cyano group, hydroxyl group, nitro group, carboxy group Etc.
  • an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and further, specific examples that are preferable in the description of each substituent Preferred substituents are preferred.
  • the term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • R 1 and R 6 are represented by the general formula (2).
  • L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted divalent residue of an aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted It is preferably a divalent residue of an unsubstituted heterocyclic group having 5 to 30 ring atoms, and L 1 , L 2 and L 3 are all single bonds.
  • the divalent residue of the aryl group having 6 to 30 ring carbon atoms is the ring in R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • Examples thereof include a divalent group derived from an aryl group having 6 to 30 carbon atoms.
  • the divalent residue of the heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • a divalent group derived from a heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • a divalent group derived from a heterocyclic group having 5 to 30 ring atoms examples thereof include a divalent group derived from an aryl group having 6 to 30 carbon atoms.
  • the divalent residue of the heterocyclic group having 5 to 30 ring atoms is represented by R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula
  • Ar 1 is a monovalent residue derived from the ring structure represented by the general formula (4).
  • X is an oxygen atom or a sulfur atom, and it is preferable that it is an oxygen atom.
  • R 11 to R 18 are each independently R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). This is the same as that described in.
  • R 18 is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and more preferably a substituted aryl group having 6 to 30 ring carbon atoms. preferable.
  • R 11 to R 18 is a substituted aryl group having 6 to 30 ring carbon atoms.
  • the aryl group having 6 to 30 ring carbon atoms include those described for R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1).
  • Examples of the substituent of the aryl group having 6 to 30 ring carbon atoms have been described in R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). Things.
  • an alkyl group having 1 to 30 carbon atoms is preferable. Particularly preferred are a methyl group, an ethyl group, and an isopropyl group.
  • R 18 is more preferably a substituted phenyl group, and a phenyl group having a substituent at the ortho position. More preferred is a phenyl group having an alkyl group having 1 to 30 carbon atoms as a substituent at the ortho position. Most preferably, R 18 is a phenyl group having a group selected from a methyl group, an ethyl group, and a propyl group as a substituent at the ortho position.
  • the steric bulk around the site represented by the general formula (4) increases, and the steric exclusion effect works, so that the emission wavelength of the aromatic amine derivative of the present invention tends to be shortened. is there.
  • the bulkiness of the site represented by the general formula (4) increases, the luminous efficiency of the aromatic amine derivative of the present invention tends to be improved.
  • R 11 to R 18 is a single bond that bonds to L 1 .
  • the structure of the general formula (4) is, for example, as shown in the following general formula (4A) to general formula (4D). is there.
  • the general formula (4A) indicates that the portion of R 11 in the general formula (4) is a single bond, and does not indicate that it is a methyl group. This also applies to the other general formulas (4B) to (4D).
  • general formula (4A) when R 11 is a single bond is preferable.
  • R 18 is preferably a substituted aryl group having 6 to 30 ring carbon atoms.
  • R 11 and R 12 among the combinations of R 11 and R 12, R 12 and R 13, R 13 and R 14, R 15 and R 16, R 16 and R 17 and R 17 and R 18, at least one One or a combination may form a saturated or unsaturated ring.
  • Examples of the case where such a ring may be formed in the general formula (4) include the following general formulas (4E), (4F), and (4G).
  • R 11 to R 20 are independently from R 2 to R 5 and R 7 to R 10 in the general formula (1). The same as described. However, in the following general formulas (4E), (4F), and (4G), one of R 11 to R 20 is a single bond bonded to L 1 .
  • Ar 2 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, or the general formula ( It is a monovalent residue derived from the ring structure represented by 4) and is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • the aryl group and heterocyclic group of Ar 2 are the same as those described for R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). .
  • Ar 2 is, when a monovalent residues derived from a ring structure represented by the general formula (4), out of the R 11 to R 18, one for L 2 It is a single bond that binds. Further, when Ar 2 is represented by any one of the general formulas (4E), (4F), and (4G), R 11 to R 20 in the general formulas (4E), (4F), and (4G) Of these, one is a single bond that bonds to L 2 .
  • Ar 2 is preferably an unsubstituted phenyl group or a phenyl group substituted with an alkyl group having 1 to 30 carbon atoms.
  • the ortho position is preferably a phenyl group substituted with an alkyl group having 1 to 30 carbon atoms, and the ortho position is a methyl group or More preferred is a phenyl group substituted with an ethyl group.
  • aromatic amine derivative of the present invention examples include the following. However, the present invention is not limited to aromatic amine derivatives having these structures.
  • the compounds represented by the general formula (2) have the same structure as each other.
  • the present invention is not limited to this. It may be a compound having a different structure.
  • the aromatic amine derivative of the present invention can be used as a material for an organic EL device.
  • the material for an organic EL device may contain the aromatic amine derivative of the present invention alone or may contain other compounds.
  • the material for organic EL elements containing the aromatic amine derivative of the present invention can be used as a dopant material, for example.
  • a material for an organic EL device including an anthracene derivative represented by the general formula (20) can be given.
  • the organic EL element material which contains the pyrene derivative represented by following General formula (30) with the aromatic amine derivative of this invention instead of this anthracene derivative is mentioned.
  • the organic EL element material containing the aromatic amine derivative of this invention, the anthracene derivative represented by the said General formula (20), and the pyrene derivative represented by the following general formula (30) is mentioned.
  • the organic EL device of the present invention includes an organic compound layer between a cathode and an anode.
  • the aromatic amine derivative of the present invention is contained in this organic compound layer.
  • an organic compound layer is formed using the material for organic EL elements containing the aromatic amine derivative of this invention.
  • the organic compound layer has at least one organic thin film layer composed of an organic compound. At least one of the organic thin film layers contains the aromatic amine derivative of the present invention alone or as a component of a mixture.
  • the organic thin film layer may contain the inorganic compound. At least one of the organic thin film layers is a light emitting layer.
  • the organic compound layer may be composed of, for example, a single light emitting layer, such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, an electron barrier layer, etc. You may have the layer employ
  • the aromatic amine derivative of the present invention is contained alone or as a component of the mixture in at least one of the layers.
  • the light emitting layer contains the aromatic amine derivative of the present invention.
  • the light emitting layer can be composed of only an aromatic amine derivative, or can be composed of an aromatic amine derivative as a host material or a dopant material.
  • the configuration (e) is preferably used, but it is not limited thereto.
  • the “light emitting layer” is an organic layer having a light emitting function, and includes a host material and a dopant material when a doping system is employed.
  • the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
  • hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”
  • electron injection / transport layer means “an electron injection layer and an electron transport layer”. "At least one of them”.
  • the positive hole injection layer is provided in the anode side.
  • the electron injection layer is provided in the cathode side.
  • the hole injection layer, the light emitting layer, and the electron injection layer may each be formed of two or more layers.
  • the layer that injects holes from the electrode is a hole injection layer
  • the layer that receives holes from the hole injection layer and transports holes to the light emitting layer is a hole transport layer.
  • a layer that injects electrons from an electrode is referred to as an electron injection layer
  • a layer that receives electrons from the electron injection layer and transports electrons to a light emitting layer is referred to as an electron transport layer.
  • the “barrier layer” is adjacent to the light emitting layer.
  • the barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the electron transport band, and increases the density of the triplet excitons by confining the triplet excitons in the light emitting layer. It has a function of efficiently causing a phenomenon that singlet excitons are generated by collisional fusion of excitons, that is, a TTF (triplet-triplet fusion) phenomenon.
  • the barrier layer also has a role of efficiently injecting electrons into the light emitting layer. When the electron injecting property to the light emitting layer is lowered, the density of triplet excitons is reduced by reducing the electron-hole recombination in the light emitting layer. When the density of the triplet exciton is reduced, the collision frequency of the triplet exciton decreases, and the TTF phenomenon does not occur efficiently.
  • the organic EL element can prevent the brightness
  • a light emitting material, a doping material, a hole injection material, and an electron injection material can be used in combination.
  • light emission luminance and light emission efficiency may be improved.
  • Each of these layers is selected and used depending on factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.
  • the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic compound layer 10 disposed between the anode 3 and the cathode 4.
  • the organic compound layer 10 includes a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, a barrier layer 8, and an electron injection layer 9 in order from the anode 3 side.
  • the light emitting layer of the organic EL element has a function of providing a field for recombination of electrons and holes and connecting this to light emission.
  • the aromatic amine derivative of the present invention is contained in at least one layer of the organic thin film layer, and is further represented by the anthracene derivative represented by the general formula (20) and the following general formula (30). It is preferable that at least one of pyrene derivatives is contained.
  • the light emitting layer contains the aromatic amine derivative of the present invention as a dopant material and an anthracene derivative represented by the above formula (20) as a host material.
  • Ar 11 and Ar 12 are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms or a condensed or unsubstituted ring atom having 10 to 30 ring atoms. It is a group composed of a ring group or a combination of the monocyclic group and the condensed ring group.
  • the monocyclic group is a group composed of only a ring structure having no condensed structure.
  • the number of ring-forming atoms of the monocyclic group is 5 to 30, preferably 5 to 20.
  • the monocyclic group include aromatic groups such as phenyl group, biphenyl group, terphenyl group, and quarterphenyl group, and heterocyclic groups such as pyridyl group, pyrazyl group, pyrimidyl group, triazinyl group, furyl group, and thienyl group. Is mentioned. Among these, a phenyl group, a biphenyl group, and a terphenyl group are preferable.
  • the condensed ring group is a group in which two or more ring structures are condensed.
  • the number of ring-forming atoms of the fused ring group is 10-30, preferably 10-20.
  • Examples of the condensed ring group include naphthyl group, phenanthryl group, anthryl group, chrysenyl group, benzoanthryl group, benzophenanthryl group, triphenylenyl group, benzochrysenyl group, indenyl group, fluorenyl group, 9,9-dimethylfluorene group.
  • Nyl group benzofluorenyl group, dibenzofluorenyl group, fluoranthenyl group, benzofluoranthenyl group and other condensed aromatic ring groups, benzofuranyl group, benzothiophenyl group, indolyl group, dibenzofuranyl group, Examples thereof include condensed heterocyclic groups such as a dibenzothiophenyl group, a carbazolyl group, a quinolyl group, and a phenanthrolinyl group.
  • naphthyl group phenanthryl group, anthryl group, 9,9-dimethylfluorenyl group, fluoranthenyl group, benzoanthryl group, dibenzothiophenyl group, dibenzofuranyl group, and carbazolyl group are preferable.
  • alkyl group, silyl group, alkoxy group, aryloxy group, aralkyl group, and halogen atom from R 101 to R 108 in the general formula (20) include R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 are the same as those described above, and the cycloalkyl group is the same as that exemplified above. Further, the case of “substituted or unsubstituted” in these substituents is the same as described above.
  • the preferable specific example in General formula (20) is given below.
  • Ar 11 and Ar 12 in the general formula (20) and preferable substituents of “substituted or unsubstituted” from R 101 to R 108 are monocyclic groups, condensed ring groups, alkyl groups, cycloalkyl groups, silyl groups. , An alkoxy group, a cyano group, and a halogen atom (particularly fluorine). Particularly preferred are a monocyclic group and a condensed ring group, and preferred specific substituents are the same as those in the general formula (20) and the general formula (1).
  • the anthracene derivative represented by the general formula (20) is preferably any of the following anthracene derivatives (A), (B), and (C), and is selected according to the configuration of the organic EL element to be applied and the required characteristics. .
  • Anthracene derivatives (A) In the anthracene derivative (A), Ar 11 and Ar 12 in the general formula (20) are substituted or unsubstituted condensed ring groups having 10 to 30 ring atoms.
  • the anthracene derivative (A) is divided into a case where Ar 11 and Ar 12 are the same substituted or unsubstituted condensed ring group and a case where Ar 11 and Ar 12 are different substituted or unsubstituted condensed ring groups. be able to.
  • Ar 11 and Ar 12 are different, the case where the substitution positions are different is also included.
  • an anthracene derivative in which Ar 11 and Ar 12 in the general formula (20) are different substituted or unsubstituted condensed ring groups is particularly preferable.
  • preferred specific examples of the condensed ring group in Ar 11 and Ar 12 in the general formula (20) are as described above. Of these, naphthyl group, phenanthryl group, benzoanthryl group, fluorenyl group, 9,9-dimethylfluorenyl group and dibenzofuranyl group are preferable.
  • Ar 12 is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, and a dibenzofuranyl group, and Ar 11 is a substituted or unsubstituted fluorenyl group. Can be mentioned.
  • Anthracene derivatives (B)
  • one of Ar 11 and Ar 12 in the general formula (20) is a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring.
  • a condensed ring group having 10 to 30 atoms.
  • Ar 12 is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, a fluorenyl group, a 9,9-dimethylfluorenyl group, and a dibenzofuranyl group, and Ar 11 is , An unsubstituted phenyl group, or a case in which at least one of the monocyclic group and the condensed ring group is a substituted phenyl group.
  • specific groups of preferred monocyclic groups and condensed ring groups are as described above.
  • anthracene derivative (B) includes a case where Ar 12 is a substituted or unsubstituted condensed ring group having 10 to 30 ring atoms and Ar 11 is an unsubstituted phenyl group.
  • the condensed ring group is particularly preferably a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a benzoanthryl group.
  • Anthracene derivatives (C) are each independently a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms.
  • a preferred form of the anthracene derivative (C) includes a case where Ar 11 and Ar 12 are each independently a substituted or unsubstituted phenyl group.
  • Ar 11 is an unsubstituted phenyl group
  • Ar 12 is a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • Ar 11 and Ar 12 are each independently a phenyl group having at least one of the monocyclic group and the condensed ring group as a substituent.
  • the monocyclic group as a substituent is more preferably a phenyl group or a biphenyl group
  • the condensed ring group as a substituent is a naphthyl group, a phenanthryl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, a benzoan group.
  • a tolyl group is more preferred.
  • anthracene derivative represented by the general formula (20) include the following. However, the present invention is not limited to the anthracene derivatives having these structures.
  • R 101 and R 105 are each independently a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted group.
  • a condensed ring group having 10 to 30 ring atoms a group composed of a combination of a monocyclic group and a condensed ring group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon
  • Ar 51 and Ar 54 each independently represent a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. It is a fused ring divalent residue of ⁇ 30.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 are each independently a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 51 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 52 and Ar 55 each independently represent a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 represents a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 is a single bond, a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a condensed having 10 to 30 ring atoms that are substituted or unsubstituted. It is a ring divalent residue.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 represents a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted condensed ring divalent having 10 to 30 ring atoms.
  • Ar 55 represents a single bond, a substituted or unsubstituted monovalent divalent residue having 5 to 30 ring atoms, or a condensed having 10 to 30 ring atoms that are substituted or unsubstituted. It is a ring divalent residue.
  • Ar 53 and Ar 56 are each independently a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 52 and Ar 55 are each independently a single bond, a substituted or unsubstituted monocyclic divalent residue having 5 to 30 ring atoms, or a substituted or unsubstituted ring. It is a condensed ring divalent residue having 10 to 30 atoms.
  • Ar 53 and Ar 56 each independently represent a hydrogen atom, a substituted or unsubstituted monocyclic group having 5 to 30 ring atoms, or a substituted or unsubstituted ring atom having 10 atoms. 30 to 30 condensed ring groups.
  • Ar 12 in the general formula (20) is selected from a naphthyl group, a phenanthryl group, a benzoanthryl group, and a dibenzofuranyl group, and Ar 11 is a substituted or unsubstituted phenyl group, Or what is a substituted or unsubstituted fluorenyl group is preferable.
  • anthracene derivatives include the following. However, the present invention is not limited to the anthracene derivatives having these structures. Of the specific structures of the following anthracene derivatives, in the compounds EM36, EM44, EM77, EM85, EM86, etc., the line extending from the 9th position of the fluorene ring represents a methyl group, that is, the fluorene ring is 9 , 9-dimethylfluorene ring.
  • a line extending in a cross shape outward from the ring structure is a tertiary butyl group. Represents.
  • a line extending from the silicon atom (Si) represents a methyl group, that is, the substituent having the silicon atom represents a trimethylsilyl group.
  • At least one of the organic thin film layers comprises an aromatic amine derivative represented by the general formula (1) and a pyrene derivative represented by the following general formula (30).
  • the form to contain is mentioned.
  • the light emitting layer preferably contains an aromatic amine derivative as a dopant material and a pyrene derivative as a host material.
  • Ar 111 and Ar 222 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
  • L 1 and L 2 each independently represent a substituted or unsubstituted divalent aryl group or heterocyclic group having 6 to 30 ring carbon atoms.
  • m is an integer of 0 to 1
  • n is an integer of 1 to 4
  • s is an integer of 0 to 1
  • t is an integer of 0 to 3.
  • L 1 or Ar 111 is bonded to any one of 1 to 5 positions of pyrene
  • L 2 or Ar 222 is bonded to any of 6 to 10 positions of pyrene.
  • Ar 111 and Ar 222 in the general formula (30) and the case of “substituted or unsubstituted” in the substituents of L 1 and L 2 are the same as described above.
  • L 1 and L 2 in the general formula (30) are preferably A substituted or unsubstituted phenylene group, A substituted or unsubstituted biphenylene group, A substituted or unsubstituted naphthylene group, It is selected from a substituted or unsubstituted terphenylene group, a substituted or unsubstituted fluorenylene group, and a divalent aryl group composed of a combination of these groups.
  • M in the general formula (30) is preferably an integer of 0 to 1.
  • n is preferably an integer of 1 to 2.
  • s is preferably an integer of 0 to 1.
  • T in the general formula (30) is preferably an integer of 0 to 2.
  • the aryl groups of Ar 111 and Ar 222 in the general formula (30) are described in R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9 and R 10 in the general formula (1). It is the same as what I did.
  • the aryl group include a phenyl group, a naphthyl group, a phenanthryl group, a fluorenyl group, a biphenyl group, an anthryl group, and a pyrenyl group.
  • the aromatic amine derivative of the present invention in addition to the light emitting layer, a hole injection layer, a hole transport layer, It can also be used for an electron injection layer and an electron transport layer.
  • Examples of materials other than the general formula (20) and the general formula (30) that can be used in the light emitting layer together with the aromatic amine derivative of the present invention include naphthalene, phenanthrene, rubrene, anthracene, tetracene, pyrene, perylene, chrysene, Condensed polycyclic aromatic compounds such as decacyclene, coronene, tetraphenylcyclopentadiene, pentaphenylcyclopentadiene, fluorene, spirofluorene and their derivatives, organometallic complexes such as tris (8-quinolinolato) aluminum, triarylamine derivatives, styryl Amine derivatives, stilbene derivatives, coumarin derivatives, pyran derivatives, oxazone derivatives, benzothiazole derivatives, benzoxazole derivatives, benzimidazole derivatives,
  • the organic thin film layer contains the aromatic amine derivative of the present invention as a dopant material
  • the content of the aromatic amine derivative is preferably 0.1% by mass or more and 20% by mass or less, and preferably 1% by mass or more and 10% by mass. The following is more preferable.
  • the organic EL element of the present invention is produced on a light-transmitting substrate.
  • the translucent substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm or more and 700 nm or less of 50% or more.
  • the substrate preferably further has mechanical and thermal strength.
  • a glass plate, a polymer plate, etc. are mentioned.
  • the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
  • the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
  • a polymer film can also be used as the substrate.
  • a material having a work function larger than 4 eV is suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum Further, palladium, etc. and their alloys, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used.
  • the anode is produced by forming a thin film of these conductive materials by a method such as vapor deposition or sputtering.
  • the light transmittance in the visible region of the anode be greater than 10%.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness of the anode depends on the material, it is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
  • the conductive material used for the cathode of the organic EL device of the present invention those having a work function smaller than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum , Lithium fluoride and the like and alloys thereof are used, but not limited thereto.
  • alloys include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but are not limited thereto.
  • the ratio of the alloy is controlled by the temperature of the vapor deposition source, the atmosphere, the degree of vacuum, etc., and is selected to an appropriate ratio.
  • the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
  • the aspect which takes out light emission from a cathode side is also employable.
  • the light transmittance in the visible region of the cathode be greater than 10%.
  • the sheet resistance of the cathode is preferably several hundred ⁇ / ⁇ or less.
  • the layer thickness of the cathode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 50 nm to 200 nm.
  • the anode and the cathode may be formed with a layer structure of two or more layers if necessary.
  • the organic EL device of the present invention in order to emit light efficiently, it is desirable that at least one surface be sufficiently transparent in the light emission wavelength region of the device.
  • the substrate is also preferably transparent.
  • the transparent electrode is set using the above-described conductive material so that predetermined translucency is ensured by a method such as vapor deposition or sputtering.
  • a hole injection material a compound having the ability to transport holes, the hole injection effect from the anode, the hole injection effect excellent for the light emitting layer or the light emitting material, and the thin film forming ability Is preferred.
  • a more effective hole injection material is a phthalocyanine derivative.
  • phthalocyanine (Pc) derivatives examples include H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO) AlPc, (HO) GaPc, VOPc, and OPP Examples include, but are not limited to, phthalocyanine derivatives and naphthalocyanine derivatives such as MoOPc and GaPc-O-GaPc.
  • carriers can be sensitized by adding an electron acceptor such as a TCNQ derivative to the hole injection material.
  • a preferred hole transport material that can be used in the organic EL device of the present invention is an aromatic tertiary amine derivative.
  • the aromatic tertiary amine derivative include N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N, N ′, N′-tetra Biphenyl-1,1′-biphenyl-4,4′-diamine or the like, or an oligomer or polymer having an aromatic tertiary amine skeleton is not limited thereto.
  • the following electron injection materials are used for the electron injection / transport layer.
  • the electron injecting material a compound having an ability to transport electrons, an electron injecting effect from the cathode, an excellent electron injecting effect for the light emitting layer or the light emitting material, and an excellent thin film forming ability is preferable.
  • more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.
  • the metal complex compound include 8-hydroxyquinolinate lithium, bis (8-hydroxyquinolinato) zinc, tris (8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis. (10-Hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, and the like are exemplified, but not limited thereto.
  • nitrogen-containing heterocyclic derivative for example, oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine and the like are preferable, and among them, benzimidazole derivative, phenanthroline derivative, imidazopyridine Derivatives are preferred.
  • a preferred form of the organic EL device of the present invention includes a form in which at least one of an electron donating dopant and an organometallic complex is further contained in these electron injection materials. More preferably, in order to facilitate reception of electrons from the cathode, at least one of an electron donating dopant and an organometallic complex is doped in the vicinity of the interface between the organic thin film layer and the cathode. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
  • the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.
  • alkali metal examples include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • K, Rb, and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
  • alkaline earth metal examples include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV).
  • a work function of 2.9 eV or less is particularly preferable.
  • the rare earth metal examples include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
  • preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
  • alkali metal compound examples include lithium oxide (Li 2 O), cesium oxide (Cs 2 O), alkali oxides such as potassium oxide (K 2 O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine.
  • alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li 2 O), and sodium fluoride (NaF) are preferable.
  • alkaline earth metal compound examples include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba x Sr 1-x O) (0 ⁇ x ⁇ 1), Examples thereof include barium calcium oxide (Ba x Ca 1-x O) (0 ⁇ x ⁇ 1), and BaO, SrO, and CaO are preferable.
  • the rare earth metal compound ytterbium fluoride (YbF 3), scandium fluoride (ScF 3), scandium oxide (ScO 3), yttrium oxide (Y 2 O 3), cerium oxide (Ce 2 O 3), gadolinium fluoride (GdF 3), such as terbium fluoride (TbF 3) can be mentioned, YbF 3, ScF 3, TbF 3 are preferable.
  • the organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions.
  • the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
  • the electron donating dopant and the organometallic complex may be used singly or in combination of two or more.
  • Each layer of the organic EL device of the present invention can be formed by any of dry deposition methods such as vacuum deposition, sputtering, plasma, and ion plating, and wet deposition methods such as spin coating, dipping, flow coating, and inkjet. can do.
  • the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like to form a thin film, and any solvent may be used.
  • an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane or the like
  • any solvent may be used.
  • an organic EL material-containing solution containing the aromatic amine derivative of the present invention and a solvent can be used as a material for an organic EL element.
  • an appropriate resin or additive may be used for improving the film formability and preventing pinholes in the film.
  • the film thickness is not particularly limited, but must be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. If the film thickness is too thin, pinholes and the like are generated, and sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the normal film thickness is suitably in the range of 5 nm to 10 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display, a light source such as a copying machine, a printer, a backlight of a liquid crystal display or an instrument, a lighting device, a display board, a marker lamp, and the like.
  • the compound of this invention can be used not only in an organic EL element but in fields, such as an electrophotographic photoreceptor, a photoelectric conversion element, a solar cell, an image sensor.
  • the present invention is not limited to the above-described embodiment, but includes modifications and improvements as long as the object of the present invention can be achieved.
  • a light emitting material in addition to at least one selected from the aromatic amine derivatives represented by the general formula (1), a light emitting material, a doping material, a hole injection material, At least one of the hole transport material and the electron injection material may be contained in the same layer.
  • a protective layer is provided on the surface of the device, or the entire device is protected by silicon oil, resin, etc. It is also possible to do.
  • the configuration of the organic EL element is not limited to the configuration example of the organic EL element 1 shown in FIG.
  • an electron transport layer may be provided on the cathode side of the barrier layer, and an electron barrier layer may be provided on the anode side of the light emitting layer.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is preferable that at least one light emitting layer contains the aromatic amine derivative of the present invention.
  • the other light emitting layer may be a fluorescent light emitting layer that includes a fluorescent light emitting material and emits fluorescence, or may be a phosphorescent light emitting layer that includes a phosphorescent light emitting material and emits phosphorescence.
  • these light emitting layers may be provided adjacent to each other, or may be laminated via other layers (for example, charge generation layers). .
  • Synthesis Example 2 (Synthesis of Compound 2) In Synthesis Example 1 (1-3), 43 g of o-toluidine was used instead of aniline, and 30 g (0.40 mol) of Compound 2 was obtained in the same manner as in Synthesis Example 1. The powder was identified as Compound 2 by FD-MS analysis.
  • Synthesis Example 3 (Synthesis of Compound 3) Synthesis was performed in the same manner as in Synthesis Example 1 except that 2,6-dimethylphenylboronic acid was used in place of 2-methylphenylboronic acid in (1-1) of Synthesis Example 1 to obtain Compound 3.
  • Synthesis Example 4 (Synthesis of Compound 4) (4-1) Synthesis of 4- (2-isopropylphenyl) dibenzofuran In an argon atmosphere, 2-bromocumene 5.0 g, 6.4 g of dibenzofuran-4-ylboronic acid, 1.45 g of tetrakistriphenylphosphine palladium (0), 50 ml of 2M sodium carbonate aqueous solution, 63 ml of toluene, and 63 ml of 1,2-dimethoxyethane (DME) was added to the flask and heated to reflux for 8 hours. The reaction was allowed to cool and then extracted with toluene.
  • 2-bromocumene 5.0 g, 6.4 g of dibenzofuran-4-ylboronic acid, 1.45 g of tetrakistriphenylphosphine palladium (0), 50 ml of 2M sodium carbonate aqueous solution, 63
  • Synthesis Example 7 (Synthesis of Compound 7) Compound 7 was obtained in the same manner as in Synthesis Example 1 except that 3,8-diisopropyl-1,6-dibromopyrene was used in place of 1,6-dibromopyrene in Synthesis Example 1 (1-4).
  • Example 1 A 25 mm ⁇ 75 mm ⁇ 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum evaporation apparatus, and first, the compound HT-1 is vapor-deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed.
  • a compound HT-1 film having a thickness of 5 nm was formed. This HT-1 film functions as a hole injection layer.
  • compound HT-2 was vapor-deposited to form an HT-2 film having a thickness of 80 nm on the HT-1 film.
  • This HT-2 film functions as a first hole transport layer.
  • the compound HT-3 was vapor-deposited to form a 15 nm-thick HT-film on the HT-2 film.
  • This HT-3 film functions as a second hole transport layer.
  • compound BH-1 (host material) and compound 1 (dopant material) were co-evaporated at a mass ratio of 25: 5 to form a light-emitting layer having a thickness of 30 nm.
  • TB-1 was deposited on the light emitting layer to form a 20 nm thick barrier layer.
  • ET-1 as an electron transport material was vapor-deposited on this barrier layer to form an electron injection layer having a thickness of 5 nm.
  • LiF was vapor-deposited on this electron injection layer to form a 1-nm thick LiF film.
  • Metal Al was vapor-deposited on this LiF film to form a metal cathode having a thickness of 80 nm.
  • the organic EL element of Example 1 was produced.
  • Example 2 An organic EL device was produced in the same manner as in Example 1 except that Compound 1 was changed to Compound 2 in Example 1.
  • Example 3 An organic EL device was produced in the same manner as in Example 1 except that Compound 1 was changed to Compound 3 in Example 1. Comparative example 1 In Example 1, the organic EL element was produced similarly to Example 1 except having changed the compound 1 into the comparative compound.
  • Example 4 An organic EL element was produced in the same manner as in Example 1 except that TB-1 was changed to TB-2 in Example 1.
  • Example 5 An organic EL device was produced in the same manner as in Example 3 except that Compound 1 was changed to Compound 2 in Example 4.
  • Example 6 An organic EL device was produced in the same manner as in Example 3 except that Compound 1 was changed to Compound 3 in Example 4. Comparative example 2 In Example 4, the organic EL element was produced similarly to Example 3 except having changed the compound 1 into the comparative compound.
  • the organic EL device using compounds 1 to 3 having a phenyl group substituted with an alkyl group as a substituent is compared with the organic EL device using a comparative compound having an unsubstituted phenyl group. It can be seen that the y value of the color purity is small, the peak wavelength is at a short wavelength, and light emission with high color purity is obtained. In addition, the device using the compounds 1 to 3 emits light with higher efficiency than the device using the comparative compound. This is also because the substituent added to the phenyl group contributes to the efficiency improvement.
  • Example 7 an organic EL device was prepared in the same manner as in Example 1 except that HT-4 was used instead of HT-2, HT-5 was used instead of HT-3, and Compound 4 was used instead of Compound 1. Initial performance was measured. The results are shown in Table 3.
  • Example 7 In Example 7, except that the compound 4 was changed to a comparative compound, an organic EL device was produced in the same manner as in Example 7, and the initial performance was measured. The results are shown in Table 3.
  • Example 8 Examples 8 to 10 and Comparative Example 4
  • HT-4 was used instead of HT-2
  • HT-5 was used instead of HT-3
  • TB-2 was used instead of TB-1
  • the dopant materials listed in the table were used instead of Compound 1.
  • the organic EL device of the present invention can be used for a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.
  • a flat light emitter such as a flat panel display of a wall-mounted television, a copying machine, a printer, a light source such as a backlight of a liquid crystal display or instruments, a display board, a marker lamp, and the like.

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Abstract

L'invention concerne des dérivés d'amine aromatique représentés par la formule générale (1). Dans la formule générale (1), R2 à R5, R7 à R9 et R10 représentent chacun un atome d'hydrogène ou un substituant. R1 et R6 dans la formule générale (1) sont représentés par la formule générale (2), dans laquelle L1 à L3 sont chacun une simple liaison ou similaire. Dans la formule générale (2), Ar1 représente un reste monovalent issu de la structure cyclique représentée par la formule générale (4) ; X représente un atome d'oxygène ou un atome de soufre ; et au moins l'un de R11 à R18 représente un groupe alkyle substitué. Dans la formule générale (2), Ar2 représente un groupe aryle ou un reste monovalent ou similaires issu de la structure cyclique représentée par la formule générale (4).
PCT/JP2012/080319 2011-11-25 2012-11-22 Dérivé d'amine aromatique, matière pour élément électroluminescent organique et élément électroluminescent organique Ceased WO2013077406A1 (fr)

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US9818953B2 (en) 2017-11-14

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